5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-L-lyxono-1,4-lactone | 864948-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-L-lyxono-1,4-lactone
• 英文别名: (3aR,6S,6aR)-6-(azidomethyl)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• CAS: 864948-00-5
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: RKRSTEFOZJZVAG-CCGCGBOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-L-lyxono-1,4-lactone 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,4R,5S)-5-(azidomethyl)-N-benzyl-3,4-dihydroxyoxolane-3-carboxamide
  参考文献：
  名称：

  来自支链糖内酯的支链四氢呋喃α，α-二取代-δ-糖氨基酸支架：折叠家族的一个新家族？

  摘要：

  有效的开环三羟基三氟甲磺酸盐的S N 2闭环（其中的离去基团位于与季中心相邻的伯碳上）可从支链碳水化合物内酯获得具有支链碳链的四氢呋喃；描述了新型的支链四氢呋喃α，α-二取代-δ-糖氨基酸支架的第一实例。

  DOI：

  10.1016/j.tetlet.2005.06.029
• 作为产物：
  描述：

  (3aR,6S,6aR)-6-(azidomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 在 溴 、 二异丁基氢化铝 、 potassium carbonate 、 barium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-L-lyxono-1,4-lactone
  参考文献：
  名称：

  来自支链糖内酯的支链四氢呋喃α，α-二取代-δ-糖氨基酸支架：折叠家族的一个新家族？

  摘要：

  有效的开环三羟基三氟甲磺酸盐的S N 2闭环（其中的离去基团位于与季中心相邻的伯碳上）可从支链碳水化合物内酯获得具有支链碳链的四氢呋喃；描述了新型的支链四氢呋喃α，α-二取代-δ-糖氨基酸支架的第一实例。

  DOI：

  10.1016/j.tetlet.2005.06.029

文献信息

• Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds
  作者：Michela I. Simone、Alison A. Edwards、George E. Tranter、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.12.012

  日期：2008.12

  The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3R,4R,5S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by all efficient intramolecular displacement of a highly hindered neopentyl triflate allows access to enantiopure THF derivatives which have carbon substituents. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2
  作者：Michela I. Simone、Raquel G. Soengas、Sarah F. Jenkinson、Emma L. Evinson、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/j.tetasy.2012.03.007

  日期：2012.3

  Homochiral piperidines containing a quaternary carbon branch at C-2 of the piperidine ring may be made from readily available carbohydrate lactones containing a branched 2-C-hydroxymethyl substituent. This gives an easy access to the branched iininosugars. In particular a trihydroxypipecolic acid analogue, (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid, has been synthesised efficiently from the starting material D-ribose and (35,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol was found to be a specific inhibitor of alpha-D-glucosidase from Bacillus Stearothermophilus with an IC50 value of 93 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
• Branched tetrahydrofuran α,α-disubstituted-δ-sugar amino acid scaffolds from branched sugar lactones: a new family of foldamers?
  作者：Michela Iezzi Simone、Raquel Soengas、Christopher R. Newton、David J. Watkin、George W.J. Fleet

  DOI：10.1016/j.tetlet.2005.06.029

  日期：2005.8

  leaving group is on a primary carbon adjacent to a quaternary centre—provides access to tetrahydrofurans with branched carbon chains from branched carbohydrate lactones; the first examples of a new class of branched chain tetrahydrofuran α,α-disubstituted-δ-sugar amino acid scaffolds are described.

  有效的开环三羟基三氟甲磺酸盐的S N 2闭环（其中的离去基团位于与季中心相邻的伯碳上）可从支链碳水化合物内酯获得具有支链碳链的四氢呋喃；描述了新型的支链四氢呋喃α，α-二取代-δ-糖氨基酸支架的第一实例。